Aza-annulation of enaminones with itaconic anhydride: Kinetic preference for exocyclic enamide products

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 20, 1998, Pages 3437-3441

  Hadden, Mark ^a   Nieuwenhuyzen, Mark ^a   Potts, Deirdre ^a   Stevenson, Paul J ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748487175     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a805256e     Document Type: Article

References (25)

1. For a review, see J. d'Angelo, D. Desmaele, F. Dumas and A. Guingant, Tetrahedron: Asymmetry, 1992, 3, 459.
2. For recent example, see J. C. F. Alves, A. B. C. Simas, P. R. R. Costa and J. d'Angelo, Tetrahedron: Asymmetry, 1997, 8, 1963;
3. D. Desmaele, K. Mekouar and J. d'Angelo, J. Org. Chem., 1997, 62, 3890;
4. J. d'Angelo, C. Cave, D. Desmaele, A. Gassama, C. Thominiaux and C. Riche, Heterocycles, 1998, 37, 725.
5. For a review, see J. R. Stille and Nancy S. Barta, Stud. Nat. Prod. Chem., 1996, 18, 315.
6. For recent examples, see K. Paulvannan and J. R. Stille, J. Org. Chem., 1992, 57, 5319;
7. K. Paulvannan and J. R. Stille, J. Org. Chem., 1994, 59, 1613;
8. G. R. Cook, L. G. Beholz and J. R. Stille, J. Org. Chem., 1994, 59, 3575;
9. L. G. Beholz, P. Benovsky, D. L. Ward, N. S. Barta and J. R. Stille, J. Org. Chem., 1997, 62, 1033;
10. A. Guarna, C. Belle, F. Machetti, F. Occhiato, E. G. Payne, C. Cassiani, G. Danza, A. Debellis, S. Dini, A. Marrucci and K. Serio, J. Med. Chem., 1997, 40, 1112;
11. P. Benovsky, G. A. Stephenson and J. R. Stille, J. Am. Chem. Soc., 1998, 120, 2493.
12. L. Ambroise, D. Desmaele and J. d'Angelo, Tetrahedron Lett., 1994, 35, 9705.
13. N. S. Barta, A. Brode and J. R. Stille, J. Am. Chem. Soc., 1994, 116, 6201.
14. H. Matsuyama, Y. Ebisawa, M. Kobayashi and N. Kamigata, Heterocycles, 1989, 29, 449.
15. P. W. Hiekmott and G. Sheppard, J. Chem. Soc. C, 1971, 2112;
16. A. Sevin, J. Tortajada and M. Pfau, J. Org. Chem., 1986, 51, 2671.
17. J. H. Robson and E. Marcus, Chem. Ind. (London), 1970, 1022;
18. H. von Bobeneck, E. Brunner, H. Bunke, G. Metzner, R. Schmidt, E. Weil and J. Sonnenbichler, Liebigs. Ann. Chem., 1981, 410.
19. C. Cave, A. Gassama, J. Mahuteau, J. d'Angelo and C. Riche, Tetrahedron Lett., 1997, 38, 4773;
20. J. d'Angelo, C. Cave and D. Desmaele, Isr. J. Chem., 1997, 37, 81.
21. F. G. Fang and S. J. Danishefsky, Tetrahedron Lett., 1989, 28, 3621;
22. T. Nagasaka, H. Inque, M. Ichimura and F. Hamaguchi, Synthesis, 1982, 848.
23. F. Johnston, Chem. Rev., 1968, 68, 375;
24. R. W. Hoffmann, Chem. Rev., 1989, 89, 1841.
25. C. Cave, V. Daley, J. d'Angelo and A. Guingant, Tetrahedron: Asymmetry, 1995, 6, 79.